We investigate thermalization dynamics of a driven dipolar many-body quantum system through the stability of discrete time crystalline order. Using periodic driving of electronic spin impurities in diamond, we realize different types of interactions between spins and demonstrate experimentally that the interplay of disorder, driving, and interactions leads to several qualitatively distinct regimes of thermalization. For short driving periods, the observed dynamics are well described by an effective Hamiltonian which sensitively depends on interaction details. For long driving periods, the system becomes susceptible to energy exchange with the driving field and eventually enters a universal thermalizing regime, where the dynamics can be described by interaction-induced dephasing of individual spins. Our analysis reveals important differences between thermalization of long-range Ising and other dipolar spin models.